Road Trip Sicily Like a Local

This is an 11-Day Tailored Group Experience across Sicily for Solo Travellers!

Road Trip Sicily Like a Local

This is an 11-Day Tailored Group Experience across Sicily for Solo Travelers!

Road Trip Sicily Like a Local

This is an 11-Day Tailored Group Experience across Sicily for Solo Travelers!

Black Friday Sale | $500 OFF | promo Code: ESCAPE
Road Tryp Sicily | 11 Day Adventure | June 4-14, 2025
11 DAY ADVENTURE | FROM $3,165 USD
What to expect

How Tryps Does Sicily!

You will discover the soul of Sicily on a road trip beyond your imagination. Olivia, our Trip Leader, is an Italian-Canadian that designed this trip to take you off the beaten path. She will be personally showing you the authentic way of life in Sicily, along with locations very much appreciated by locals. 

In Taormina, a day unfolds with a guided walking tour, a visit to the ancient amphitheater, and boutique shopping. Venture to the summit of the still-active Etna Volcano, Europe's tallest, for a guided hike and a tour of a volcanic winery. Historic Ortigia invites exploration, from the town and local food markets to a dip in pristine blue waters, offering the best paninos in Sicily. You and your fellow solo travelers will spend a day on a private farm, sipping wine and mastering Sicilian cooking! The adventure will wrap up with an exploration of the islands off the coast of Trapani and the natural pearls of Zingaro. You will have experienced one of the most iconic parts of Italy that many are not lucky enough to see.

DAY

01

Welcome to Sicily!

Our team will escort you from the airport to your hotel.

Airport Pickup

Hotel Check In

Welcome Dinner

DAY

01

Welcome to Sicily!

Our team will escort you from the airport to your hotel.

Airport Pickup

Hotel Check In

Welcome Dinner

DAY

02

Explore Taormina

We’ll spend the day uncovering the magic and beauty of Taormina!

Guided Walking Tour

Ancient Amphitheatre

Boutique Shopping

DAY

02

Explore Taormina

We’ll spend the day uncovering the magic and beauty of Taormina!

Guided Walking Tour

Ancient Amphitheatre

Boutique Shopping

DAY

03

Climb the Etna Volcano

Summit the still active Etna Volcano and visit a volcanic winery.

Guided Etna Volcano Hike

Volcanic Wine Tour

Drive to Ortigia

DAY

03

Climb the Etna Volcano

Summit the still active Etna Volcano and visit a volcanic winery.

Guided Etna Volcano Hike

Volcanic Wine Tour

Drive to Ortigia

DAY

04

Historic Ortigia

Explore the town, the local food markets and swim in the pristine blue waters.

Guided Walking Tour

Best paninos in Sicily

Beach Time

DAY

04

Historic Ortigia

Explore the town, the local food markets and swim in the pristine blue waters.

Guided Walking Tour

Best paninos in Sicily

Beach Time

DAY

05

San Lorenzo Beach Club

Dive into the crystal clear waters of the Mediterranean Sea.

Visit the town of Noto

San Lorenzo Beach Club

Explore Marzamemi

DAY

05

San Lorenzo Beach Club

Dive into the crystal clear waters of the Mediterranean Sea.

Visit the town of Noto

San Lorenzo Beach Club

Explore Marzamemi

DAY

06

Valley of the Temples

Discover the temples and the history of Agrigento.

Valley of the Temples

Scala Dei Turchi (Turkish Steps)

Sunset on the Beach

DAY

06

Valley of the Temples

Discover the temples and the history of Agrigento.

Valley of the Temples

Scala Dei Turchi (Turkish Steps)

Sunset on the Beach

DAY

07

Sicilian Culinary Experience

Spend the day on your private farm, sipping wine and learning to cook like a Sicilian.

Relax by your private pool

Private Cooking Workshop

Olivia Radocchia

“Sicily is like a whole world unto itself!”

DAY

07

Sicilian Culinary Experience

Spend the day on your private farm, sipping wine and learning to cook like a Sicilian.

Relax by your private pool

Private Cooking Workshop

Olivia Radocchia

“Sicily is like a whole world unto itself!”

DAY

08

Island Hopping

Spend the day exploring the islands of the coast of Trapani.

3 Island Visits

Visit Macari

Transfer to Castellammare Del Golfo

DAY

08

Island Hopping

Spend the day exploring the islands of the coast of Trapani.

3 Island Visits

Visit Macari

Transfer to Castellammare Del Golfo

DAY

09

The Natural Pearls of Zingaro

Visit this stunning natural reserve filled with hikes and beaches.

Hike to Riserva dello Zingaro

Crystal Clear Water

Visit the Hidden Coves

DAY

09

The Natural Pearls of Zingaro

Visit this stunning natural reserve filled with hikes and beaches.

Hike to Riserva dello Zingaro

Crystal Clear Water

Visit the Hidden Coves

DAY

10

Palermo

Explore Sicily’s cultural capital - Palermo.

Farewell Lunch

Explore the town of Palermo

Anti-Mafia Tour

DAY

10

Palermo

Explore Sicily’s cultural capital - Palermo.

Farewell Lunch

Explore the town of Palermo

Anti-Mafia Tour

DAY

11

Journey Back Home

Return home with a full belly, a tanned face and deep love for the island of Sicily.

Hotel check out

Airport drop off

Flight Home

DAY

11

Journey Back Home

Return home with a full belly, a tanned face and deep love for the island of Sicily.

Hotel check out

Airport drop off

Flight Home

What’s Included

Arrival (and departure) airport transfer

Entrance Fees, Reservations for all sites

Certified tour guide for all historic sites

All Breakfast Meals; 4 Lunches; 3 Dinners

Accommodations (2 guests per room)

Stay in hand-picked hotels and Agro-Tourismos

Private air-conditioned coach bus

Local SIM Card with calling, texting and data

24/7 On-Site Support

Dietary Accommodations

Branded Tryps Backpack

Dedicated Content Creator to capture the experience so you don’t have to!

Extra Perks

Flight Booking Assistance

Packing Checklist

Online Orientation Session with your Tryp Leader

Direct Contact with your Tryp Leader through email, text and calls to answer your questions

Remember, flights aren't included and prices are based on sharing a twin room. Single room upgrades are available.
ROUTE

DAY 1

Arrive in Catania

DAY 2

Explore Taormina

DAY 3

Hike the Etna Volcano

DAY 4

Historic Ortigia

DAY 5

San Lorenzo Beach Club

DAY 6

Scala Dei Turchi (Turkish Steps)

DAY 7

Sicilian Culinary Experience

DAY 8

Island Hopping 

DAY 9

The Natural Pearls of Zingaro

DAY 10

Farewells in Palermo

DAY 11

Depart Back Home

Next Trip

June 4-14, 2025

Sites You Will See in Italy

Accommodations

Boutique hotels along the water and ago turismo in the countryside.

FAQs

Got More Questions?

Click here to chat directly with one of our Tryp Leaders.
book a call

Next Trip

June 4-14, 2025